US3620712A - Single phase composition - Google Patents
Single phase composition Download PDFInfo
- Publication number
- US3620712A US3620712A US786761A US3620712DA US3620712A US 3620712 A US3620712 A US 3620712A US 786761 A US786761 A US 786761A US 3620712D A US3620712D A US 3620712DA US 3620712 A US3620712 A US 3620712A
- Authority
- US
- United States
- Prior art keywords
- composition
- methyl
- ester
- percent
- polyethoxylated sorbitan
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 66
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 30
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 28
- 239000000194 fatty acid Substances 0.000 claims abstract description 28
- 229930195729 fatty acid Natural products 0.000 claims abstract description 28
- 150000004702 methyl esters Chemical class 0.000 claims abstract description 23
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Polymers OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 claims description 33
- -1 fatty acid ester Chemical class 0.000 claims description 31
- JNYAEWCLZODPBN-UHFFFAOYSA-N 2-(1,2-dihydroxyethyl)oxolane-3,4-diol Polymers OCC(O)C1OCC(O)C1O JNYAEWCLZODPBN-UHFFFAOYSA-N 0.000 claims description 27
- JNYAEWCLZODPBN-CTQIIAAMSA-N sorbitan Polymers OCC(O)C1OCC(O)[C@@H]1O JNYAEWCLZODPBN-CTQIIAAMSA-N 0.000 claims description 27
- JGHZJRVDZXSNKQ-UHFFFAOYSA-N methyl octanoate Chemical group CCCCCCCC(=O)OC JGHZJRVDZXSNKQ-UHFFFAOYSA-N 0.000 claims description 20
- YRHYCMZPEVDGFQ-UHFFFAOYSA-N methyl decanoate Chemical compound CCCCCCCCCC(=O)OC YRHYCMZPEVDGFQ-UHFFFAOYSA-N 0.000 claims description 18
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 16
- 239000005641 Methyl octanoate Substances 0.000 claims description 10
- 239000005640 Methyl decanoate Substances 0.000 claims description 9
- 150000004665 fatty acids Chemical class 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- IJXHLVMUNBOGRR-UHFFFAOYSA-N methyl nonanoate Chemical compound CCCCCCCCC(=O)OC IJXHLVMUNBOGRR-UHFFFAOYSA-N 0.000 claims description 6
- 239000007822 coupling agent Substances 0.000 claims description 3
- 229940049964 oleate Drugs 0.000 claims description 2
- 239000003995 emulsifying agent Substances 0.000 abstract description 14
- 150000002148 esters Chemical class 0.000 abstract description 9
- 239000000839 emulsion Substances 0.000 description 11
- 241000196324 Embryophyta Species 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 7
- 229920001213 Polysorbate 20 Polymers 0.000 description 4
- 241000208422 Rhododendron Species 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 4
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- 231100000674 Phytotoxicity Toxicity 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000000442 meristematic effect Effects 0.000 description 2
- NUKZAGXMHTUAFE-UHFFFAOYSA-N methyl hexanoate Chemical compound CCCCCC(=O)OC NUKZAGXMHTUAFE-UHFFFAOYSA-N 0.000 description 2
- 229920000136 polysorbate Polymers 0.000 description 2
- 125000005472 straight-chain saturated fatty acid group Chemical group 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- FAHUKNBUIVOJJR-UHFFFAOYSA-N 1-(4-fluorophenyl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine Chemical compound C1=CC(F)=CC=C1C1C2=CC=CN2CCN1 FAHUKNBUIVOJJR-UHFFFAOYSA-N 0.000 description 1
- 241000208140 Acer Species 0.000 description 1
- 240000003870 Ageratum houstonianum Species 0.000 description 1
- 240000001436 Antirrhinum majus Species 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- 235000010910 Betula neoalaskana Nutrition 0.000 description 1
- 244000274847 Betula papyrifera Species 0.000 description 1
- 235000021508 Coleus Nutrition 0.000 description 1
- 244000061182 Coleus blumei Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 240000006497 Dianthus caryophyllus Species 0.000 description 1
- 235000009355 Dianthus caryophyllus Nutrition 0.000 description 1
- 241000555682 Forsythia x intermedia Species 0.000 description 1
- 241000208152 Geranium Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000299507 Gossypium hirsutum Species 0.000 description 1
- 241000721662 Juniperus Species 0.000 description 1
- 241001513379 Kolkwitzia Species 0.000 description 1
- 241000735234 Ligustrum Species 0.000 description 1
- 241000245240 Lonicera Species 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 244000070406 Malus silvestris Species 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 240000001987 Pyrus communis Species 0.000 description 1
- 235000014443 Pyrus communis Nutrition 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 241001116500 Taxus Species 0.000 description 1
- 241001326149 Weigela Species 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 239000002361 compost Substances 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 235000005489 dwarf bean Nutrition 0.000 description 1
- 244000013123 dwarf bean Species 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000001856 mountain paper birch Nutrition 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 235000001842 paper birch Nutrition 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 230000008654 plant damage Effects 0.000 description 1
- 230000008121 plant development Effects 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01D—HARVESTING; MOWING
- A01D25/00—Lifters for beet or like crops
- A01D25/04—Machines with moving or rotating tools
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01D—HARVESTING; MOWING
- A01D23/00—Topping machines
- A01D23/04—Topping machines cutting the tops after being lifted
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
Definitions
- compositions which when diluted with water form stable emulsions suitable for application to plants to kill meristematic tissue without damaging mature tissue or subsequent'plant growth. (E.g., as chemical "pinching" agents for ornamental plants, trees and flowers.)
- Such compositions are prepared at a central location and sold to the eventual user who prepares a more dilute aqueous emulsion. Accordingly it is desirable to have single phase compositions which are homogeneous on a molecular scale to ermit the eventual user to accurately measure the amount of material being used. It is also esthetically desirable to have a clear single phase composition.
- compositions of this invention which are suitable for dilution with water to form emulsions for use as chemical pinching agents for plants consist essentially of: v
- A a mixture of 1. methyl ester of straight chain saturated fatty acid containing from about six to about 12 carbon atoms and 2. fatty acid ester of polyethoxylated sorbitan wherein the fatty acid contains from about ten to about l8 carbon atoms and wherein there are from about five to about 80 ethoxy moieties per molecule; the ratio of said methyl esters to said fatty acid esters of polyethoxylated sorbitan being from about 3:1 to about 121.2; and A B. as a coupling agent to make said composition clear and single-phase, from about 4 percent to about 16 percent of water by weight of the total composition.
- the gsource of the fatty acids used is not critical and can be either a inaturalsource such as coconut oil or a synthetic source.
- the emulsifiers for the methyl esters in the aqueous emul- ISIOIIS (chemical pinching agents) formed from the concentrated compositions of this invention are fatty acid esters of polyethoxylated"sorbitan.
- Suitable fatty acids useful in forming the esters of polyethoxylated sorbitan include: decanoic, undecanoic, dodecanoic, tridecanoic, tetradecanoic, pentadecanoic, hexadecanoic, heptadecanoic, octadecanoic, and octadecanoic acids or mixtures thereof.
- ethoxy moieties per molecule are preferred for ease of formulation and efi'ectiveness of the diluted composition as hereinafter described as a chemical pinching agent.
- Preferred emulsifiers which give the most stable emulsions for use as chemical pinching agents with minimum plant damage (phytotoxicity) are: dodecanoate ester of polyethoxylated sorbitan containing an average of about 20 ethoxy moieties per Qmolecule; oleate-ester of polyethoxylated sorbitan containing an average of about 20 ethoxy moieties per molecule; and Idodecanoate ester of polyethoxylatd sorbitan containing an gaverage of about five ethoxy moieties per molecule.
- the most preferred emulsifier is the dodecanoate ester of polyethoxylated sorbitan containing an average of about 20 ethoxy moieties per molecule.
- the preferred ratio of methyl ester to emulsifier is from about 2:1 to about 1:12 and the most preferred ratiois about 1:1. These ratios are preferred for maximum pinching at minimum phytotoxicity.
- the preferred amount of water is from about 6 percent to about 12 percent by weight of the composition and the most preferred amount is about 10 percent by weight of the composition.
- These arnounts of water allow leeway in formulation w 'tt qsstetsrss s a s-r lesa ts r
- the compositions of this invention can be readily diluted with water, either by adding water to the composition or by adding the composition to water for form stable aqueous emulsions containing from about 2 percent to'ab'out 12 per .cent of the methyl ester.
- emulsions are especially adapted for application to a wide variety of shrubs, trees and ,flowers for the purpose of killing meristematic tissue and ithereby accomplishing the pinching" without adverse effect ion mature tissues or subsequent plant development.
- plants which can be treated are: ageratum, coleus, cotton, Imarigold, peanut, snapbean, snapdragon, soybean, tomato, carnation, chrystanthemum, forsythia, geranium, apple, azalea, chamecyparis, elm, eyonymous, juniper, kolkwitzia, ligustrum, lonicera, maple, paper birch, pyrancantha, taxus, weigela and pear.
- compositions l7 and 18 are outside the scope of this invention and contain two phases despite the fact that they are only just outside the limits.
- fatty acid ester of polyethoxylated sorbitan wherein the which h y indicating the P t more than :fatty acid contains from about 10 to.about 18 carbon atoms one Ph were tftta'ted at room temperature wlth water to Qand wherein there are from about five to about 80 ethoxy the Polht of cleanhg mto one Phase and on to the next moieties per molecule; the ratio of said methyl esters to said Point whell'e the P 8 became ctoudy- 4o fatty acid esters of polyethoxylated sorbitan being from about 3:1 to about l:l.2;and ;B. as a coupling agent to make said composition clear and single-phase, from about 4 percent to about 16 percent of water Percent water t by weight of the total composition.
- composition of claim 1 wherein the methyl ester is 20 selected from the group consisting of methyl octanoate,
- the fatty acid ester of lfiil tsyl tl polyethoxylated sorbitan is selected from the group consisting M51151 est er'fif 15551115; of dodecanoate ester of polyethoxylated sorbitan containing z ffig g --6 5.8 6.3 an average of about 20 ethoxy moieties per molecule; oleate ester of polyethoxylated sorbitan containing an average of about 20 ethoxy moieties per molecule; and dodecanoate ester of polyethoxylated sorbitan containing an average of about five ethoxy moieties per molecule.
- composition of claim 1 wherein the ratio of methyl
- the above data indicate that within the range of from about 4 Percent to about 16 p l' y Weight fthe compost ester to fatty acid ester of polyethoxylated sorbitan is about tion, it is possible to clarify mixtures of methyl esters and fatty acid esters of polyethoxylated sorbitan (emulsifier) as herein-
- the composition of claim 1 containing from about 6 before described. However, it should be noted that with some cent to about 12 percent water. of the emulsifier/methyl ester combinations, the range of the 6.
- composition of claim 1 wherein the methyl ester is amou t O Water q Couple y) the composition selected from the group consisting of methyl decanoate and is smaller than the range from about 4 percent to about 16 mixtures f methyl decanoate and methyl octanoate i Petceht y Weight of the composition Accoldihgly a certain ing no more than 75 percent by weight of methyl octanoate. amount of variation can be expected within the broad range
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Environmental Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US78676168A | 1968-12-24 | 1968-12-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3620712A true US3620712A (en) | 1971-11-16 |
Family
ID=25139520
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US786761A Expired - Lifetime US3620712A (en) | 1968-12-24 | 1968-12-24 | Single phase composition |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3620712A (enrdf_load_stackoverflow) |
| JP (1) | JPS5312573B1 (enrdf_load_stackoverflow) |
| BE (1) | BE743533A (enrdf_load_stackoverflow) |
| DE (1) | DE1964959A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1267109A (enrdf_load_stackoverflow) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3888656A (en) * | 1973-12-17 | 1975-06-10 | Dow Chemical Co | Chemical tree-pruning method |
| US3888654A (en) * | 1973-04-05 | 1975-06-10 | Akzona Inc | Tobacco sucker control |
| US3900307A (en) * | 1973-04-05 | 1975-08-19 | Akzona Inc | Composition and method for controlling suckers in tobacco |
| US3989502A (en) * | 1973-10-27 | 1976-11-02 | Sumitomo Chemical Company, Limited | Method for controlling growth of tobacco suckers |
| WO1983003041A1 (en) * | 1982-03-03 | 1983-09-15 | Biochemical Marketing Corp | Plant growth stimulators comprising metal ions and long-chain alkyl carboxylic acids and salts and derivatives thereof |
| US4556410A (en) * | 1981-03-10 | 1985-12-03 | Minnesota Mining And Manufacturing Company | Compositions for tobacco sucker growth control |
| US4557751A (en) * | 1981-03-10 | 1985-12-10 | Minnesota Mining And Manufacturing Company | Compositions containing surfactant and broadleaf foliar herbicide |
| WO1994024858A1 (en) * | 1993-05-05 | 1994-11-10 | Victorian Chemical International Pty. Ltd. | Herbicide, crop desiccant and defoliant adjuvants |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3014875A1 (de) * | 1980-04-17 | 1981-10-22 | Siemens AG, 1000 Berlin und 8000 München | Kontakttraeger |
| DE3033335A1 (de) * | 1980-09-04 | 1982-04-22 | Lentia GmbH Chem. u. pharm. Erzeugnisse - Industriebedarf, 8000 München | Verfahren zur herstellung einer lagerstabilen, konzentrierten emulsion von herbizid wirkenden phenoxyalkancarbonsaeureestern |
| BE1006376A3 (fr) * | 1992-11-24 | 1994-08-09 | Fina Research | Compositions concentrees et leur utilisation pour le pincage chimique du houblon. |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3057804A (en) * | 1958-05-28 | 1962-10-09 | Foster D Snell Inc | All-weather surface cleaner |
| US3326664A (en) * | 1964-01-10 | 1967-06-20 | Tien C Tso | Method of tobacco sucker control |
| US3340040A (en) * | 1964-01-10 | 1967-09-05 | Tien C Tso | Method of tobacco sucker control |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3619168A (en) * | 1967-07-24 | 1971-11-09 | Emery Industries Inc | Method for killing undesirable plant growth |
-
1968
- 1968-12-24 US US786761A patent/US3620712A/en not_active Expired - Lifetime
-
1969
- 1969-12-22 BE BE743533D patent/BE743533A/xx not_active IP Right Cessation
- 1969-12-22 GB GB1267109D patent/GB1267109A/en not_active Expired
- 1969-12-24 JP JP10351069A patent/JPS5312573B1/ja active Pending
- 1969-12-24 DE DE19691964959 patent/DE1964959A1/de not_active Withdrawn
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3057804A (en) * | 1958-05-28 | 1962-10-09 | Foster D Snell Inc | All-weather surface cleaner |
| US3326664A (en) * | 1964-01-10 | 1967-06-20 | Tien C Tso | Method of tobacco sucker control |
| US3340040A (en) * | 1964-01-10 | 1967-09-05 | Tien C Tso | Method of tobacco sucker control |
Non-Patent Citations (4)
| Title |
|---|
| Jansen et al., Effects of Surfactants on the Herb. Act. etc.; (1961) Weeds, Vol. 9, No. 3, pp. 381 384 and 390. * |
| McCutcheon, Detergents & Emulsifiers 1966 Ann., p. 210 (1966) TP990 D4 * |
| Temple et al., The Effect of Surfactants on the Water Sal. etc., (1963) Weeds, Vol. 11, No. 4, pp. 297 300 (1963) * |
| Tso et al., Inhibition of Tobacco Axillary Bad Growth, etc., (1965) J. Ag. Food Chem. 13, pp. 78 81 (1965) * |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3888654A (en) * | 1973-04-05 | 1975-06-10 | Akzona Inc | Tobacco sucker control |
| US3900307A (en) * | 1973-04-05 | 1975-08-19 | Akzona Inc | Composition and method for controlling suckers in tobacco |
| US3989502A (en) * | 1973-10-27 | 1976-11-02 | Sumitomo Chemical Company, Limited | Method for controlling growth of tobacco suckers |
| US3888656A (en) * | 1973-12-17 | 1975-06-10 | Dow Chemical Co | Chemical tree-pruning method |
| US4556410A (en) * | 1981-03-10 | 1985-12-03 | Minnesota Mining And Manufacturing Company | Compositions for tobacco sucker growth control |
| US4557751A (en) * | 1981-03-10 | 1985-12-10 | Minnesota Mining And Manufacturing Company | Compositions containing surfactant and broadleaf foliar herbicide |
| WO1983003041A1 (en) * | 1982-03-03 | 1983-09-15 | Biochemical Marketing Corp | Plant growth stimulators comprising metal ions and long-chain alkyl carboxylic acids and salts and derivatives thereof |
| WO1994024858A1 (en) * | 1993-05-05 | 1994-11-10 | Victorian Chemical International Pty. Ltd. | Herbicide, crop desiccant and defoliant adjuvants |
| GB2291595A (en) * | 1993-05-05 | 1996-01-31 | Victorian Chemical Internation | Herbicide,crop desiccant and defoliant adjuvants |
| US5631205A (en) * | 1993-05-05 | 1997-05-20 | Victorian Chemical International Pty. Ltd. | Herbicide, crop desiccant and defolliant adjuvants comprising an unsaturated fatty acid ethyl ester and a non-ionic emulsifier |
| GB2291595B (en) * | 1993-05-05 | 1997-05-28 | Victorian Chemical Internation | Herbicide,crop desiccant and defoliant adjuvants |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1964959A1 (de) | 1970-07-09 |
| BE743533A (enrdf_load_stackoverflow) | 1970-06-22 |
| JPS5312573B1 (enrdf_load_stackoverflow) | 1978-05-02 |
| GB1267109A (enrdf_load_stackoverflow) | 1972-03-15 |
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